Listener Stacy is mulling over a marriage proposal. History and tradition suggest that’s the ultimate romantic expression. But at our age, does it make financial sense? For help answering that question, Laura calls on two experts: certified financial planner Colette Kolanko; and attorney Laurie Israel, author of “The Generous Prenup: How to Support Your Marriage and Avoid the Pitfalls.” 

Stacy’s wondering whether she should walk down the aisle or maintain status quo.

Financial planner Colette Kolanko has personal experience with the money/marriage issue. (photo by Jared Wolfe)



I kind of feel sorry for younger people when they get married because I know why we cry at weddings.


Your one listener who said something about her now fiancé really wants to get married. Is it about finances, or is it about the blessing?


That’s a prenup attorney and a certified financial planner, talking about marriage. They both have longtime partners, by the way, and not that anyone’s overly focused on the bottom line. But now that we’re older, we might need to be wiser. When it comes to walking down the aisle, love isn’t the only consideration. “Maybe I Do.” That’s this episode of Dating While Gray: The Grown-Up’s Guide to Love, Sex, and Relationships. I’m Laura Stassi.

When history and tradition suggests that marriage is the ultimate romantic commitment, it can be hard to take a different path.

STACY 01:06

My name is Stacy, and I’m from Milwaukee, Wisconsin. My boyfriend of about four years asked me to marry him. I love him. And I want to be committed, I have no problem being in the relationship with him for a long time, if not forever. But I was worried about finances for each of us in the future. It’s taken me a long time to be where I’m at financially. And I’m very proud of it. And not that my boyfriend would do anything. But my ex-husband was very bad at finances and destroyed our credit. I know that my boyfriend isn’t that but I’m just really proud and I don’t see where it would change anything in our relationship. It’s very strong. We’re very much together. And I was just wondering if you had anything or any show about this. Thank you.


Thank you, Stacy. She was game to share her story but we had technical difficulties recording her. So I called to get more details. Stacy told me she was married for over 30 years. Her husband was the main earner and he was very controlling. He kept a tight grip on their finances even as he mismanaged their money. They wound up losing their home to bankruptcy. Stacey waited until their three kids were launched and then said, enough. When she left her husband, there wasn’t really anything to divide. She had a car and a car payment — and that was about it. Stacy was on shaky financial footing, but she felt unburdened because she was finally in charge of her own destiny. She landed a good-paying job and eventually started dating.

Stacy really clicked with one man who had been divorced for a while. They became exclusive and then he moved in. After a year of living in her place and sharing expenses, they found a bigger place to rent together. Stacy says they’re completely transparent with each other about finances. So she knows they each have about the same amount of money, and they each earn about the same amount. They split the bills and Stacy’s the admin for their shared expenses.

hen Stacy’s partner first brought up marriage, she kind of surprised herself by saying maybe instead of yes. Stacy’s comfortable with the concept. It’s familiar to her. She appreciates being asked. And apparently, he keeps asking. Stacy says she never wants marriage off the table. You heard Stacy say, though, she doesn’t think marriage will change anything. I think she’s referring to their emotional connection and level of commitment. Because when it comes to our financial picture, marriage can change a lot of things. That’s according to experts like Colette Kolanko. She’s a certified financial planner and a certified divorce financial analyst.


There are a multitude of financial impacts of having that status of married, may affect somebody’s finances and a financial reason to get married.


It’s not a yes or no question.


Absolutely not.


Unless we’re really savvy, we might not be able to figure it out ourselves, whether it makes sense.




Financially makes sense.


Correct. Sometimes you want to talk to these professionals, just to gather the information so that you can make that informed decision. You can know if you get married and in the eyes of the government, if  that is going to cost you or if it’s going to benefit you financially.


Maybe you remember Colette from the “Money Talk” episode in 2020. She described a legal document I’d never heard of before — a cohabitation agreement. Colette also mentioned that every year, she and her longtime fiancée crunch the numbers to figure out if it makes financial sense for them to go ahead and tie the knot. I asked Colette to share more of her professional insights for this episode. And as you’ll hear, she also has a personal update.


Here’s a scenario. You’re 64, getting ready to retire, you have this huge pension, you meet the love of your life. And when it comes time to take this pension, you can say, oh, I can put my spouse on the pension and they can receive the benefit. There’s a whole bunch of things that go through that. So if you’re not married, usually, there’s no option to have a non-spouse. So that might be one consideration.

Taxes might be a reason. You could either — maybe someone has a very small income and somebody has really large income. And if you were able to put them together as married filing jointly, the combined taxes would go down significantly. Those are the issues that I as a financial planner would look at as financial reasons to get married.

Some people say I don’t care what it costs. I love this person, I want to marry them. But from a financial aspect, and a protection aspect, what are the pros of getting married later in life? If somebody has a large IRA, and their partner is more than 10 years younger than they are, their required distribution calculation is different,


The first thing is, we should all get an estate plan. Regardless, if we never intend to get married, if we’re not dating anybody. That seems like that’s the baseline.


Right, base, base, baseline. And it’s not really all that expensive. The way I look at an estate plan is, you’ve got this bucket. And at the end of your life, you’re going to say, I want a portion to go here, I want a portion to go there. The package that I think of, also, are your powers of attorney, who can make medical decisions for you. That’s a medical power of attorney. If something should happen to you, who can make financial decisions on your behalf. That’s a financial power of attorney.


Let’s say as a single person, go ahead and do this. I’ve got a house. And you know, I want to leave the house to my kids, I want to make sure that my kids are my medical power of attorney, I want to make sure my kids are my financial power of attorney, get it all in place, and then I meet the love of my life. If we were to get married, would we have to alter any of those documents? Or do those documents still stay in place?


That’s a legal question. Honestly, right now, I know two different situations where someone is in the exact same place, had their financial powers of attorney and their medical powers of attorney. And then they got married. And because the doctors had on file that somebody else was responsible for making the medical decisions, they’re not talking to the spouse. First of all, I would say, if you’re considering getting married, you should evaluate for both of you. You should update your estate documents.

My partner and I, he proposed in 2001. And of course, I said yes. And then as we were starting to go down the planning process, I said, well, here, this is what we’re going to pay in taxes. Here are my numbers, you go take it to your CPA, and you can clarify that. And so he takes the numbers, goes talks to his CPA, he comes back and he goes,  I love you too much to marry you also.

So every year, I have done our taxes. And we have decided, okay, let’s not get married this year. Now full disclosure, my friends and family know that we are discussing, he’s coming up to a point in time where Medicare costs are coming in. And his IRA, I’m more than 10 years younger than he is. So his required distribution would be less. You don’t have to say no forever, or I’m not going to marry you forever, because of financial reasons. I mean, things change, they always change. But we evaluated So, by the time you hear this, it could be married, or it could not be. We’ve been engaged now for 23 years.

I think it’s fabulous that people can find each other after they have gone through trials and tribulations. And I think that in order to make sure that remains that fabulous relationship, you want to put as many protections, safeguards in place as you can. And these are just tools. When you see a financial planner, and you get a plan, or you look at your investments, and you have people helping you invest, you talk to an attorney, these are just tools. And they’re the building blocks that just help to prop you up in hard times, and good times, right, so that you can go forward and continue to build that relationship.


Okay, quick recap. Regardless of relationship status, bank account size, and how much stuff we have, we all need at least a basic estate plan. That means a will and medical and financial powers of attorney.


This is one of the best gifts that you can give your loved ones. Put all this in place so that when your time comes, your family, your beneficiaries, your loved ones, they have a direction as to what to do.


Thanks, Colette. So maybe you’re in a relationship and you go through the spreadsheets, and marriage makes financial sense. Or maybe it doesn’t, but you want to go ahead and do it anyway. Nothing wrong with that, as long as everyone’s eyes are wide open. But before you take that next step, you may want to consider, well, you probably know what I’m going to say. The P word, prenup.


So the process can be really bad. But it shouldn’t be. It should be good if you’re going to have a prenup.


That’s attorney and mediator Laurie Israel. We’ll hear more from her. Plus another listener talks about the financial commitment she made with a romantic partner. That’s all after the break.


GIGI 12:17

Hi, Laura. My name is Gigi. I’m loving your podcast. It’s so comforting to hear each other’s stories. You’re wonderful. Here’s my story. I dated a guy long distance, he lived three hours away for four years. So we saw each other a lot. We then bought a house together and became legal domestic partners. I worked for a city agency and he owns his own business. He was paying high premiums for his insurance, medical. So I put him on my benefits. Because we were legal domestic partners, he was able to get my medical —  hospital, prescription optical.

And marriage was never discussed. I don’t think either of us wanted to again, domestic partners was fine. We each had our own bank accounts and handled our finances separately. We had a joint account for shared bills like the mortgage, utilities, home purchases like furniture or Costco run. We did this for four years, eight years total in relationship math. And it worked beautifully. I thought he was the love of my life.

But then I had the rug pulled from under me. He decided to end things. I had had a slip and fall, which resulted in surgeries, many doctor’s appointments he had to take time out of his life to drive me to, and also left me unable to do many of the activities we used to enjoy together like swimming, boating, we played music together. I couldn’t play the guitar anymore. Although it was never addressed, he just simply said we hit a wall. He wound up buying me out of the house. It was my idea. And maybe not the best one monetarily because maybe I could have made a little more had we sold the house. Maybe not. I don’t know. Emotionally, I felt like I could not survive another day there. I believe I couldn’t.

I think I made the best choice for me emotionally. So even though finances were never a problem with us and all the financial safety nets in place, the breakup was very, very difficult for me. I had approved myself to move, I was with my what I thought was my happily ever after. I was totally rejected. And on top of that, the stress of a move was very painful. And yeah, I guess it was as painful as a divorce. Although no little children was involved. It was very painful. Well I’m gonna say goodbye. Thank you, Laura. You be well, too.


Thanks, Gigi, for sharing your story. So obviously, being clear about money doesn’t guarantee a happily ever after. But according to Laurie Israel, for older couples contemplating marriage, a prenup can help us on that path. Laurie is an attorney and a mediator based in Massachusetts. She began her career as a tax lawyer, but for the past several years has focused on prenups and post ups. She’s become nationally recognized in the field.

Laurie emphasizes the process of creating a prenup, so it doesn’t cause emotional damage to a relationship. And she says younger couples and first marriages may not even need one. Laurie has written a book called ,”The Generous Prenup: How to Support Your Marriage and Avoid the Pitfalls.”


I’m really glad you read the book.


Well, I have to tell you, I left finishing that book thinking, not why anybody would get a prenup, but why anybody would get married? Why would I, seriously?


Oh, no. I thought it was very pro-marriage.


Well, I don’t think it makes a lot of sense. I mean, when you think about marriage, I think a lot of us even as we’re older we think of marriage as love. I left the book thinking okay, marriage is a legal contract with someone else. And to undo that legal contract, whether through divorce or through death, oh my gosh, I don’t think people realize.


That’s what a prenup does, it makes an orderly dissolution at divorce or death. It actually helps. You know, as I say, I’m not a pro prenup person. But I think for second marriages, it can be extremely useful.


As a legal spouse, do they have a certain status that supersedes the grown kids’ status in your life?


If you die without a will, in most states, what happens is that — and you have children from a previous marriage. In most states, your assets would go half to your new wife and half to your kids. But most people have wills and the wills do overcome the prenup. Unless the prenup has a requirement for estate planning, or some sort of floor for estate planning, I recommend that. I think it’s really important because somebody could kind of get demented at the end and think that their wife or husband is having an affair and takes them out of their will. And so my prenups also have a minimum requirement, or no requirement if people don’t need one. But some sort of minimal requirement, and that minimum requirement does hold because the prenup is basically a contractual debt obligation.


So I know we should enter into prenups with the best of intentions, like I love you so much. I want to make sure you’re protected in case I die. But with older people, are you still putting in things about in case they get divorced?


LAURIE ISRAEL Oh, yeah, there’s a divorce provision too, absolutely. Sometimes a provision that talks about how they’re going to handle money during their marriage, which sometimes it’s important. There’s a divorce provision because sometimes people get divorced, and there’s a death provision.


Let’s say you’re a committed couple. And you verbally agree, okay, I’m going to keep my income and assets separate. You keep your income and assets separate. Should you decide to get married, would you still need a prenup?


I think you do. I think you do need a prenup when you get married, and one of the reasons is for divorce, because you can have any sort of verbal agreement that nothing holds for divorce. I think working through the process in terms of what you’re going to do when one of you dies. And having that written, I think that’s really important. There’s all sorts of financial decisions which you can make without a prenup. But, you know, the other part of it is that when people get married late in life, and you’re 63, I wouldn’t call you late in life, you’re middle-aged.


Thank you. I agree.



You know, there’s kind of a delicate issue about how the children will feel about your marriage, especially if you’re going to marry somebody younger. And then that raises some issues. Because if you’re going to protect your younger spouse, then that delays what could possibly have come to your children earlier. Thinking about how children feel about it, and how to present the prenup to children — not that you’d show it to them. But, you know, sometimes you’d want to tell your children that, I’ve thought about you.


Could you put in your prenup something along the lines of, I want my children to have a say in your medical power of attorney, as opposed to your spouse? Is something like that going to fly?


There’s going to be a separate document that’s going to be the health care proxy, the health care agency, that’s a separate thing. But if you’re sure you want your children to be your healthcare proxy and to have other powers, then it would be good to have that in as a disclosure and the prenup say something like, each of us can name each other or children or any other person as our healthcare proxy and power of attorney, whatever.


Okay, so a prenup is more like one tool in the estate planning arsenal that older couples should do.


Right. You’d have to do an estate plan. A prenup is not an estate plan. It’s a contractual agreement that creates a debt obligation.

In my view, in my wisdom of my 77 years, I think that living together without marriage only goes so far. And there’s also some good financial reasons. I mean, this is maybe a piddling financial reason. If you’re married, and your spouse dies, and he or she has higher Social Security than you, you can step into his or her shoes and get their Social Security not yours. Plus, there’s that that’s really significant. For a lot of women spouses.

You know, part of the problem with prenups, it’s the process tends to be so bad, I found a really good way to do it. And that is, I do them by mediation. And I actually, because I’m a mediator, I do it all over the country. And what I do is, I work with a couple, we get all the financial documents securely, that we can all see. We discuss them, we talk about their aims, we talk about their issues or financial issues. It’s a little bit like financial psychotherapy, although I’m not a psychotherapist.

We end up with a term sheet that they both feel good about. And then I usually try to locate lawyers in their state, which are usually collaborative divorce lawyers because they understand marriages. And you know, the problem with attorneys and prenups is they want to protect somebody’s assets, but they’re very unproductive of the health of the marriage — which requires, you know, looking at both parties and trying to figure out what is fair and secure on both sides.


It almost sounds like you’re a prenup doula.


That’s so good. That’s maybe my next book.


Thanks, Laurie. And I feel like I have to apologize for sounding so anti-marriage. I think I was feeling that way because a prenup for older couples does seem like a no-brainer. And crafting a prenup, even under the best of processes, requires potentially uncomfortable conversations. You know, what if and if then, blah, blah, blah.

But it’s dawned on me that I’m not anti-coupling up. And when I meet the next love of my life, in order to put our best feet forward together, those what-if and if-then conversations are really important, no matter which avenue we choose for expressing our romantic commitment.


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I’m Laura Stassi. Thanks so much for listening.

 Episode transcripts are posted on the Dating While Gray website before they are thoroughly proofread. The audio of this episode is the authoritative record. For terms of use and permissions, please email

Episode transcripts are posted on the Dating While Gray website before they are thoroughly proofread. The audio of this episode is the authoritative record. For terms of use and permissions, please email